CA1268891A - Methode de preparation de polyisocyanates bloques renfermant des groupes carbodiimide; polyisocyanates ainsi obtenus et leur emploi pour la fabrication de plastiques - Google Patents

Methode de preparation de polyisocyanates bloques renfermant des groupes carbodiimide; polyisocyanates ainsi obtenus et leur emploi pour la fabrication de plastiques

Info

Publication number: CA1268891A
Authority: CA; Canada
Prior art keywords: groups; isocyanate groups; isocyanate; production; blocked
Prior art date: 1986-01-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA000526458A

Other languages

English (en)

Inventor

Willi Dunwald

Reinhard Halpaap

Josef Pedain

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-01-14

Filing date

1986-12-30

Publication date

1990-05-08

1986-12-30 Application filed by Bayer AG filed Critical Bayer AG

1990-05-08 Application granted granted Critical

1990-05-08 Publication of CA1268891A publication Critical patent/CA1268891A/fr

2007-05-08 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 48
239000005056 polyisocyanate Substances 0.000 title claims abstract description 44
229920001228 polyisocyanate Polymers 0.000 title claims abstract description 41
238000004519 manufacturing process Methods 0.000 title claims abstract description 30
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 title abstract description 20
239000004033 plastic Substances 0.000 title abstract description 13
229920003023 plastic Polymers 0.000 title abstract description 13
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 50
150000001718 carbodiimides Chemical group 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 20
125000000879 imine group Chemical group 0.000 claims abstract description 15
239000002981 blocking agent Substances 0.000 claims abstract description 11
150000002894 organic compounds Chemical class 0.000 claims abstract description 11
230000008030 elimination Effects 0.000 claims abstract description 6
238000003379 elimination reaction Methods 0.000 claims abstract description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 52
229910002092 carbon dioxide Inorganic materials 0.000 claims description 26
238000000576 coating method Methods 0.000 claims description 20
239000000758 substrate Substances 0.000 claims description 13
239000011541 reaction mixture Substances 0.000 claims description 9
230000000903 blocking effect Effects 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
239000001569 carbon dioxide Substances 0.000 claims description 7
239000011248 coating agent Substances 0.000 claims description 7
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 5
239000011521 glass Substances 0.000 claims description 4
239000004744 fabric Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 41
239000012948 isocyanate Substances 0.000 abstract description 25
150000002513 isocyanates Chemical class 0.000 abstract description 25
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239000000376 reactant Substances 0.000 description 11
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KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000001361 adipic acid Substances 0.000 description 4
235000011037 adipic acid Nutrition 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
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XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
150000003739 xylenols Chemical class 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000001896 cresols Chemical class 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000002574 poison Substances 0.000 description 3
231100000614 poison Toxicity 0.000 description 3
239000007858 starting material Substances 0.000 description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
229920000877 Melamine resin Chemical group 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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238000007259 addition reaction Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
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125000003118 aryl group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
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238000006482 condensation reaction Methods 0.000 description 2
239000003431 cross linking reagent Substances 0.000 description 2
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
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125000005442 diisocyanate group Chemical group 0.000 description 2
238000003618 dip coating Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
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OJDSGUYSPJFSDM-UHFFFAOYSA-N S=P1=CCCC1 Chemical class S=P1=CCCC1 OJDSGUYSPJFSDM-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 1
TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 description 1
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000007084 catalytic combustion reaction Methods 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
150000002118 epoxides Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
229940035423 ethyl ether Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
150000001469 hydantoins Chemical class 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UNSDDJQNHCSVSW-UHFFFAOYSA-N n-(3,3-dimethylbutan-2-ylidene)hydroxylamine Chemical compound ON=C(C)C(C)(C)C UNSDDJQNHCSVSW-UHFFFAOYSA-N 0.000 description 1
HZCRFUPEBRNAAI-UHFFFAOYSA-N n-(3-methylbutan-2-ylidene)hydroxylamine Chemical compound CC(C)C(C)=NO HZCRFUPEBRNAAI-UHFFFAOYSA-N 0.000 description 1
ZKALVNREMFLWAN-UHFFFAOYSA-N n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)CC(C)=NO ZKALVNREMFLWAN-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
YGNXYFLJZILPEK-UHFFFAOYSA-N n-cyclopentylidenehydroxylamine Chemical compound ON=C1CCCC1 YGNXYFLJZILPEK-UHFFFAOYSA-N 0.000 description 1
NAQQTJZRCYNBRX-UHFFFAOYSA-N n-pentan-3-ylidenehydroxylamine Chemical compound CCC(CC)=NO NAQQTJZRCYNBRX-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940038384 octadecane Drugs 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000005476 soldering Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/26—Macromolecular compounds or prepolymers
- C03C25/32—Macromolecular compounds or prepolymers obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C03C25/326—Polyureas; Polyurethanes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/302—Polyurethanes or polythiourethanes; Polyurea or polythiourea

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Geochemistry & Mineralogy (AREA)
General Chemical & Material Sciences (AREA)
Materials Engineering (AREA)
Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
Polyurethanes Or Polyureas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paints Or Removers (AREA)

CA000526458A 1986-01-14 1986-12-30 Methode de preparation de polyisocyanates bloques renfermant des groupes carbodiimide; polyisocyanates ainsi obtenus et leur emploi pour la fabrication de plastiques Expired - Lifetime CA1268891A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3600766.8		1986-01-14
DE19863600766 DE3600766A1 (de)	1986-01-14	1986-01-14	Verfahren zur herstellung von carbodiimidgruppen enthaltenden, blockierten polyisocyanaten, die nach diesem verfahren erhaeltlichen polyisocyanate und deren verwendung zur herstellung von polyurethankunststoffen

Publications (1)

Publication Number	Publication Date
CA1268891A true CA1268891A (fr)	1990-05-08

Family

ID=6291759

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000526458A Expired - Lifetime CA1268891A (fr)	1986-01-14	1986-12-30	Methode de preparation de polyisocyanates bloques renfermant des groupes carbodiimide; polyisocyanates ainsi obtenus et leur emploi pour la fabrication de plastiques

Country Status (9)

Country	Link
US (1)	US5126479A (fr)
EP (1)	EP0231509B1 (fr)
JP (1)	JPH07108963B2 (fr)
AT (1)	ATE42274T1 (fr)
AU (1)	AU580200B2 (fr)
BR (1)	BR8700114A (fr)
CA (1)	CA1268891A (fr)
DE (2)	DE3600766A1 (fr)
ES (1)	ES2008671B3 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3610961A1 (de) *	1986-04-02	1987-10-08	Bayer Ag	Thermisch verformbare pur-hartschaumstoffe, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von automobilinnenverkleidung
DE3932168A1 (de) *	1989-09-27	1991-04-04	Bayer Ag	Lackpolyisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung
DE4019026A1 (de) *	1990-06-14	1991-12-19	Bayer Ag	Beschichtungsmittel und seine verwendung zur beschichtung hitzeresistenter substrate
US5574083A (en) *	1993-06-11	1996-11-12	Rohm And Haas Company	Aromatic polycarbodiimide crosslinkers
DE19524437A1 (de) *	1995-07-05	1997-01-09	Bayer Ag	Amid-/Imidgruppen-haltige blockierte Polyisocyanate für Drahtlacke
DE19611820A1 (de) *	1996-03-26	1997-10-02	Huels Chemische Werke Ag	Carbodiimidgruppen enthaltende blockierte (cyclo)aliphatische Diisocyanate, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung
TW393494B (en) *	1997-08-14	2000-06-11	Ajinomoto Kk	Curable resin composition for overcoat of flexible circuit
DE10008928A1 (de)	2000-02-25	2001-08-30	Degussa	Transparente oder pigmentierte Pulverlacke mit Vernetzern aus Hydroxyalkylamiden und blockierten, nicht aromatischen Polyisocyanaten
DE10051392A1 (de)	2000-10-17	2002-04-18	Bayer Ag	Elektroisolierlackbindemittel mit Harnstoff- und/oder Hydantoinstruktur
DE102004011791A1 (de) *	2004-03-09	2005-09-29	Degussa Ag	Verfahren zur Herstellung von Carbodiimidgruppen aufweisenden Substanzen
JP7028401B2 (ja) *	2018-02-23	2022-03-02	日清紡ケミカル株式会社	水性カルボジイミド含有液の製造方法
CN112574068A (zh) *	2020-11-17	2021-03-30	万华化学（宁波）有限公司	一种低色号高稳定性碳化二亚胺改性异氰酸酯的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3115479A (en) *	1955-12-08	1963-12-24		R oconr
US2941983A (en) *	1957-05-07	1960-06-21	Du Pont	Urethane-terminated polycarbodiimides
DE1546922A1 (de) *	1963-09-19	1970-08-13	Bayer Ag	Verfahren zur Herstellung von UEberzuegen und Lacken
US4077989A (en) *	1974-07-30	1978-03-07	Bayer Aktiengesellschaft	Process for the production of modified polyisocyanates
JPS6023695B2 (ja) *	1975-05-12	1985-06-08	日本ポリウレタン工業株式会社	部分ウレタン化脂環族カルボジイミドの製造方法
DE2819827A1 (de) *	1978-05-05	1979-11-08	Bayer Ag	Pulverfoermige ueberzugsmittel
DE2929224A1 (de) *	1979-07-19	1981-02-05	Huels Chemische Werke Ag	Herstellung von freie nco- und endstaendig mit epsilon -caprolactam blockierte nco-gruppen enthaltenden isophorondiisocyanataddukten, sowie danach hergestellte verbindungen

1986
- 1986-01-14 DE DE19863600766 patent/DE3600766A1/de not_active Withdrawn
- 1986-12-23 AT AT86117969T patent/ATE42274T1/de active
- 1986-12-23 EP EP86117969A patent/EP0231509B1/fr not_active Expired
- 1986-12-23 ES ES86117969T patent/ES2008671B3/es not_active Expired
- 1986-12-23 DE DE8686117969T patent/DE3662878D1/de not_active Expired
- 1986-12-24 AU AU67004/86A patent/AU580200B2/en not_active Ceased
- 1986-12-30 CA CA000526458A patent/CA1268891A/fr not_active Expired - Lifetime
1987
- 1987-01-13 BR BR8700114A patent/BR8700114A/pt not_active IP Right Cessation
- 1987-01-13 JP JP62004244A patent/JPH07108963B2/ja not_active Expired - Lifetime
1989
- 1989-05-15 US US07/351,683 patent/US5126479A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3662878D1 (en)	1989-05-24
ATE42274T1 (de)	1989-05-15
JPS62167748A (ja)	1987-07-24
EP0231509B1 (fr)	1989-04-19
EP0231509A1 (fr)	1987-08-12
DE3600766A1 (de)	1987-07-16
AU580200B2 (en)	1989-01-05
BR8700114A (pt)	1987-12-01
ES2008671B3 (es)	1989-08-01
JPH07108963B2 (ja)	1995-11-22
AU6700486A (en)	1987-07-16
US5126479A (en)	1992-06-30

Legal Events

Date	Code	Title	Description
2003-05-08	MKLA	Lapsed

Publication	Publication Date	Title
US4096291A (en)	1978-06-20	Melt coating composition and coating process
CA1213395A (fr)	1986-10-28	Polyurethanes a stabilite accrue en stockage
CA1130033A (fr)	1982-08-17	Compositions d'enduction
US4088637A (en)	1978-05-09	Process for the production of polycondensates containing imide groups
CA1217498A (fr)	1987-02-03	Polyisocyanates bloques, possedant une meilleure stabilite au stockage
US5126479A (en)	1992-06-30	Process for the production of blocked polyisocyanates containing carbodiimide groups, the polyisocyanates obtainable by this process and their use for the production of plastics
US4448844A (en)	1984-05-15	Heat resistant resin and process for producing the same
US4100144A (en)	1978-07-11	Process for the preparation of oligourethanes
US4505980A (en)	1985-03-19	Insulated wire
US4444845A (en)	1984-04-24	Process for the production of coatings and the use of N,N',N"-tris-(2-hydroxyethyl)-isocyanurate as additives for polyurethane based wire lacquers
CA2111927A1 (fr)	1994-06-25	Resines de polyester renfermant la fonction amine
US4447589A (en)	1984-05-08	Method for preparing polyamide-imide resin
US4507427A (en)	1985-03-26	Process for production of polyisocyanates containing at least partly blocked isocyanate groups, compounds obtainable by this process and their use in production of polyurethanes, stoving lacquers or aqueous polyisocyanate solutions or dispersions
AU7938801A (en)	2002-04-18	Electrical insulating enamel binders having a urea and/or hydantoin structure
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